New Tour Planning: The Berkshires and Southern Vermont, Part 1

In 2025, 718 Outdoors did a Vermont Tour for the first time since 2014. It was an amazing experience to be in a culture that welcomed bike tourers, as opposed to feeling like we were doing something wrong (a certain state's "upstate" comes to mind).

Vermont North Loop

Since returning from our 2025 Vermont Tour in August (which was primarily a loop of the north half of the Granite State), I have been thinking about a route that would explore southern Vermont in 2026.

In addition, there was also the gravitational pull of the Berkshires, where we had done Micro-Tours in 2017/2018. This was an area I wanted to explore again. As I was messing around on a map, I came to realize that Massachusetts was only 115 miles "tall" (I am not sure how tall I thought is was). Seeing that 115 sparked an idea. What if I could link the Metro-North Wassaic Train Station with the Berkshires, Southern Vermont...and could be actually get over to New Hampshire?

This is how Tours are born

The idea of a starting/ending at a Metro-North (NYC commuter rail line) stop really intrigues me, as it makes the trip much more accessible than if running on Amtrak, both in terms of cost, train/bike slot availability and general stress levels.

So, step one is to draw an overall route in RideWithGPS that hits the rough points I want, while staying the the 350-400 mile range. Traversing the Berkshires, doing a Green Mountain Pass, hitting Jamaica, VT (highly recommended campsite) then swinging east to New Hampshire were the rough parameters.

Heatmaps and Elevations

My next step is looking at heatmaps, elevations and campsite locations. I will keep you posted.

Note: For better or worse, I do not use AI to create my posts. This is all me, with my misspelling, poor grammar and tangential thoughts. I didn't get into this line of work to hand over my thoughts, expertise and experience to AI to spit out blog posts.